Mono- and bivalent ligands bearing mannose 6-phosphate (M6P) surrogates: Targeting the M6P/ insulin-like growth factor II receptor

David B. Berkowitz; Gourhari Maiti; Bradley D. Charette; Christine D. Dreis; Richard G. MacDonald

doi:10.1021/ol0479444

Mono- and bivalent ligands bearing mannose 6-phosphate (M6P) surrogates: Targeting the M6P/ insulin-like growth factor II receptor

David B. Berkowitz, Gourhari Maiti, Bradley D. Charette, Christine D. Dreis, Richard G. MacDonald

Research output: Contribution to journal › Article › peer-review

47 Scopus citations

Abstract

(Chemical Equation Presented) Mannose 6-phosphate mimics locked into the α-configuration and bearing hydrolase-resistant phosphate surrogates were synthesized and evaluated for binding affinity to the mannose 6-phosphate/insulin-like growth factor II receptor (M6P/IGF2R). Affinity increases as the phosphate surrogate is varied in the order malonyl ether < malonate < phosphonate. An alkene cross-metathesis approach to sought-after bivalent M6P-bearing ligands is also described. These compounds were designed to map onto biantennary sectors of high-mannose-type oligosaccharides carried by glycoprotein M6P/IGF2R ligands.

Original language	English (US)
Pages (from-to)	4921-4924
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	26
DOIs	https://doi.org/10.1021/ol0479444
State	Published - Dec 23 2004

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Chemical Equation Presented) Mannose 6-phosphate mimics locked into the α-configuration and bearing hydrolase-resistant phosphate surrogates were synthesized and evaluated for binding affinity to the mannose 6-phosphate/insulin-like growth factor II receptor (M6P/IGF2R). Affinity increases as the phosphate surrogate is varied in the order malonyl ether < malonate < phosphonate. An alkene cross-metathesis approach to sought-after bivalent M6P-bearing ligands is also described. These compounds were designed to map onto biantennary sectors of high-mannose-type oligosaccharides carried by glycoprotein M6P/IGF2R ligands.",

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AU - Berkowitz, David B.

AU - Maiti, Gourhari

AU - Charette, Bradley D.

AU - Dreis, Christine D.

AU - MacDonald, Richard G.

PY - 2004/12/23

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AB - (Chemical Equation Presented) Mannose 6-phosphate mimics locked into the α-configuration and bearing hydrolase-resistant phosphate surrogates were synthesized and evaluated for binding affinity to the mannose 6-phosphate/insulin-like growth factor II receptor (M6P/IGF2R). Affinity increases as the phosphate surrogate is varied in the order malonyl ether < malonate < phosphonate. An alkene cross-metathesis approach to sought-after bivalent M6P-bearing ligands is also described. These compounds were designed to map onto biantennary sectors of high-mannose-type oligosaccharides carried by glycoprotein M6P/IGF2R ligands.

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Mono- and bivalent ligands bearing mannose 6-phosphate (M6P) surrogates: Targeting the M6P/ insulin-like growth factor II receptor

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